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Kevin Rose
Partner at True Ventures, True Ventures

I Asked AI What to Do With the Next 5 Years of My Life

📅 Jul 28, 2026 Tim Ferriss 11 MIN 24274 VIEWS 71 SEGMENTS · 2 SPEAKERS
In this edition of The Random Show, Tim Ferriss and Kevin Rose reunite over tequila to talk Zen retreats, learning to rock climb at (almost) 50, mortality and grief, why you should stop saying "one day," AI predictions , and much more. Please enjoy! This episode is brought to you by: Incogni, which removes your personal data from the web, helping shield you from fraud, scams, and identity theft: https://Incogni.com/Tim (use code TIM at checkout and get 60% off an annual plan) Wealthfront high-yield cash account: https://Wealthfront.com/Tim New clients get 3.30% base APY from program banks...

What Kevin Rose said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Kevin Rose described using AI, specifically Claude Code with Gmail APIs, for a 20-year retrospective analysis of his angel investing, examining who made introductions, which companies he turned down that succeeded, and testing his own narratives against hard data. He said LLMs have been incredibly helpful for holistic health, mostly in avoiding disaster by checking contraindications among medications and supplements. He acknowledged AI's limits, noting it can hallucinate, but minimized risk by fact-checking across models. For investing, he finds AI valuable for running counterfactuals and scoring his decision-making. He admitted AI has negatively affected his writing motivation, comparing it to AlphaGo defeating a Go player, as AI can produce in 30 seconds what takes him 30 hours. He shared how he asked AI for career exploration ideas for the next five years, finding the answers outstanding and sharing them with friends. He emphasized that AI can provide insights that would otherwise be impossible to derive manually.

Key takeaways

  1. Rose used Claude Code with Gmail APIs to analyze 20 years of angel investing data, testing his own stories against hard numbers.
  2. He said AI can produce in 30 seconds what would take him 30 hours, draining his motivation for writing.
  3. Asking AI 'What do you think I should do in the next 5 years?' yielded outstanding career exploration ideas he shared with friends.
  4. He noted LLMs are helpful for holistic health, mostly to avoid disasters by checking contraindications among meds and supplements.

Numbers and commitments

FigureWhat it refers toTypeAt
20 years retrospective period for angel investing analysis timeline 0:15
30 seconds time for AI to produce what takes him 30 hours metric 6:27
30 hours time for him to do what AI does in 30 seconds metric 6:27
5 years timeframe for AI career exploration question timeline 7:29
10% percentage of AI insight that could inform a major life chapter metric 9:55

Chapters

  1. 0:0020-year retrospective analysis of angel investing
  2. 0:32Testing personal stories against data
  3. 2:20AI for holistic health and avoiding disasters
  4. 3:08Investing as a scorecard for thinking
  5. 5:48AI writing as a net negative
  6. 7:29Asking AI for career exploration ideas
  7. 10:43AI as a machine that never forgets

Questions asked in this interview

7
  1. 0:00What are you doing now with the eye stuff?
  2. 0:31Do you really want to do that to yourself?
  3. 1:33Well, plus, I mean, that's like last week, right?
  4. 2:05Like, what's the thing where you walked away and said, 'Damn, that was insightful, and I'm going to change my behavior,' or 'I learned something new about myself that I wouldn't have if I had not used AI'?
  5. 4:08Is that worth your time though?
  6. 6:43But it's not going to come up with the original thesis for the whole thing, right?
  7. 10:54But when you ask it open-ended personal questions in the way that you would ask a close friend, what do you think are three to five creative ways I might explore things professionally in the next 5 years?
Tim Ferriss 0:00 ↗
What are you doing now with the eye stuff?
Kevin Rose 0:02 ↗
Well, I mean, I'm more curious to hear your thoughts and predictions, frankly, because I think you're better at it. But I mean, I'm using Claude Code with Ferris APIs to do tons of like inbox analysis and stuff.
Tim Ferriss 0:15 ↗
Yeah, yeah, yeah.
Kevin Rose 0:15 ↗
Right? I'm doing a 20-year retrospective analysis of angel investing.
Tim Ferriss 0:20 ↗
Mhm.
Kevin Rose 0:20 ↗
It's like, who made what introductions? Which companies did I not reply to that ended up being successes? Which did I turn down that ended up being really important?
Tim Ferriss 0:31 ↗
Do you really want to do that to yourself?
Kevin Rose 0:32 ↗
Well, I suspected it'd be worse than it was. I actually have not — I haven't missed that many explicit opportunities. I wanted to test my own stories against data, right? Because I have all sorts of stories about why I did certain things and why certain things worked out. And I have certain stories about my batting average. And I'm like, but is it true? Really? Is it really true? Let's look at some hard numbers.
Tim Ferriss 1:01 ↗
The sad truth, and I have a buddy that wears that bracelet and you've seen me with the necklace around, that we categorize your AI and listens to you 24/7.
Kevin Rose 1:09 ↗
Yeah.
Tim Ferriss 1:10 ↗
It's about 70-ish percent that we think we know, but is actually what we know. Out of the 100% of like what we think we know, this is the truth. I said I wanted a dark chocolate bar at 7:00 p.m. It's like, no, you said it at 5:00 and you said it this way.
Kevin Rose 1:26 ↗
And you said it was milk chocolate.
Tim Ferriss 1:27 ↗
Yeah, exactly. So, it's always about 20% off from where you actually think your brain's at.
Kevin Rose 1:32 ↗
Which is brutal.
Tim Ferriss 1:33 ↗
Well, plus, I mean, that's like last week, right? If you're talking about 15 years ago.
Kevin Rose 1:38 ↗
I mean, if you listen to any genesis story of any startup, you're like, oh my god. Wait a minute now. Like, this is like a startup comic working on material, but he's been working on this one 5-minute bit so long that now he believes that's actually truth.
Tim Ferriss 1:52 ↗
Yeah.
Kevin Rose 1:52 ↗
That I mean, the sanitizing and the editing of these startup genesis stories is hilarious, and there's no reason to think that I would be or you would be exempt from it.
Tim Ferriss 2:01 ↗
Right.
Kevin Rose 2:01 ↗
Right, when you're telling your own story, even if you're just telling it to yourself.
Tim Ferriss 2:05 ↗
So, what's the number one thing that you've learned by applying AI to your life in this fashion? Like, what's the thing where you walked away and said, 'Damn, that was insightful, and I'm going to change my behavior,' or 'I learned something new about myself that I wouldn't have if I had not used AI'?
Kevin Rose 2:20 ↗
Well, I think from a holistic health perspective — by holistic I mean having enough data related to medications, supplements, predispositions, side effects, what happened to me 2 weeks ago — the LLMs have been incredibly helpful. I mean, the picture that they get and the speed with which they can deliver an answer that I can interrogate is just incredible.
Tim Ferriss 2:44 ↗
What did you learn? Like, what was the thing that you...
Kevin Rose 2:47 ↗
I mean, honestly, it's mostly avoiding disaster, right? It's like, are any of these things contraindicated with one another? Could A, B, or C explain D? And you have to keep in mind, these things can still hallucinate, but you can — I don't want to say eliminate that, but minimize it by just fact-checking across LLMs. There's that.
I would say that there's a lot of insight on, hopefully, that can translate to future decision-making related to investing, which investing for me is not just amassing more chips. What's fun about investing to me is it's a way to scorecard your thinking and decision-making. It's just a very objective way to decide if something was the right or the wrong decision. And you can fine-slice that, and there are ways that you could maybe question that, but if you're asking yourself, 'Was I thinking well last month?' That's not a very helpful question. Where do you go from there? If you're logging maybe every decision you make every day and then trying to cross-reference outcomes with blah blah blah — like, yeah, but you're never going to do that.
Tim Ferriss 3:55 ↗
Mhm.
Kevin Rose 3:56 ↗
But when you're making relatively frequent investments, you can do that. You can also run counterfactuals, right? What if I did the opposite? What if I had not sold that? What if I had kept that? What if I had done this? What if I had done that?
Tim Ferriss 4:08 ↗
Is that worth your time though? At the end of the day, you could put everything in the S&P 500 and just go to bed.
Kevin Rose 4:13 ↗
Well, there's that. I would say it's worth it to me because I find it interesting. I actually enjoy the intellectual exercise of it. But otherwise, I would say with in terms of like how AI has impacted me, I would say that the honest answer is not that much because most [__] isn't worth doing in the first place. People are finding very, very clever ways to expedite automating workflows of all different types, and doing something well does not make it important or worth doing in the first place. So, there's a lot — I think the level of [__] that is being done just at a very fast, efficient rate is skyrocketing.
Tim Ferriss 4:54 ↗
Yeah.
Kevin Rose 4:57 ↗
But simultaneously, there are definitely cases where I look back at, say, this analysis of 20 years of stuff. To do that manually would be impossible.
Tim Ferriss 5:08 ↗
Sure.
Kevin Rose 5:08 ↗
All right, it would take me a year full-time with multiple people to do that. And with a Claude Code Gmail API and leaving my computer running for a handful of hours a few times, it's like, what you get back is [__] credible. Like, it's unbelievable. And I haven't even scratched the surface.
Tim Ferriss 5:27 ↗
Yeah.
Kevin Rose 5:27 ↗
I will say also another way that AI has maybe affected my life in a net negative way — and I'm not... We have another mutual friend who maybe we shouldn't name who feels very similarly. We'll leave that out, but yeah.
Tim Ferriss 5:43 ↗
[laughter] Jesus Christ.

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Cite this transcript

APA, MLA, BibTeX
APA

Rose, K. (2026, July 28). I Asked AI What to Do With the Next 5 Years of My Life [Interview transcript]. Tim Ferriss. CEOInterviews.AI. https://ceointerviews.ai/interview/3006646/

MLA

Kevin Rose. "I Asked AI What to Do With the Next 5 Years of My Life." Tim Ferriss, 28 Jul. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3006646/.

BibTeX
@misc{rose2026_3006646,
  author       = {Kevin Rose},
  title        = {I Asked AI What to Do With the Next 5 Years of My Life},
  howpublished = {Interview transcript, Tim Ferriss. CEOInterviews.AI},
  year         = {2026},
  month        = {jul},
  url          = {https://ceointerviews.ai/interview/3006646/},
  note         = {Speaker-attributed transcript with timestamps}
}